You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:41 UTC
HMDB IDHMDB01009
Secondary Accession NumbersNone
Metabolite Identification
Common NameN-Methylnicotinium
DescriptionN-Methylnicotinium is a nicotine degradation product arising from its methylation by S-adenosylmethionine (and subsequent conversion to S-adnonsylcysteine).
Structure
Thumb
Synonyms
ValueSource
1-Methyl-3-(1-methyl-2-pyrrolidinyl)-pyridiniumHMDB
N-Methylnicotinium acetateHMDB
N-Methylnicotinium ionHMDB
Nicotine isomethiodideHMDB
Nicotine isomethonium ionHMDB
Chemical FormulaC11H17N2
Average Molecular Weight177.2661
Monoisotopic Molecular Weight177.139173554
IUPAC Name1-methyl-3-(1-methylpyrrolidin-2-yl)pyridin-1-ium
Traditional Namenicotine isomethonium ion
CAS Registry Number24554-05-0
SMILES
CN1CCCC1C1=CC=C[N+](C)=C1
InChI Identifier
InChI=1S/C11H17N2/c1-12-7-3-5-10(9-12)11-6-4-8-13(11)2/h3,5,7,9,11H,4,6,8H2,1-2H3/q+1
InChI KeyInChIKey=HIOROZIUERMMRQ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassNot Available
Sub ClassNot Available
Direct ParentAlkaloids and derivatives
Alternative Parents
Substituents
  • Nicotine
  • Alkaloid or derivatives
  • Pyrrolidinylpyridine
  • Aralkylamine
  • N-alkylpyrrolidine
  • Pyridinium
  • Pyridine
  • Heteroaromatic compound
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 mg/mLALOGPS
logP-3ALOGPS
logP-2.8ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)8.04ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area7.12 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity55.81 m3·mol-1ChemAxon
Polarizability21.01 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00515
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022367
KNApSAcK IDNot Available
Chemspider ID417
KEGG Compound IDNot Available
BioCyc IDCPD-3183
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01009
Metagene LinkHMDB01009
METLIN ID1533
PubChem Compound430
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available